WO2006110647A1 - Réactions de coiffage en polymérisation cationique ; cinétique et utilité en synthèse - Google Patents
Réactions de coiffage en polymérisation cationique ; cinétique et utilité en synthèse Download PDFInfo
- Publication number
- WO2006110647A1 WO2006110647A1 PCT/US2006/013308 US2006013308W WO2006110647A1 WO 2006110647 A1 WO2006110647 A1 WO 2006110647A1 US 2006013308 W US2006013308 W US 2006013308W WO 2006110647 A1 WO2006110647 A1 WO 2006110647A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymer
- solvent
- conjugated diene
- mol
- formula
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 title description 32
- 238000010538 cationic polymerization reaction Methods 0.000 title description 6
- 229920000642 polymer Polymers 0.000 claims abstract description 62
- 238000000034 method Methods 0.000 claims abstract description 48
- 239000002904 solvent Substances 0.000 claims abstract description 33
- 150000001993 dienes Chemical class 0.000 claims abstract description 23
- 125000002091 cationic group Chemical group 0.000 claims abstract description 15
- 230000026030 halogenation Effects 0.000 claims abstract description 12
- 238000005658 halogenation reaction Methods 0.000 claims abstract description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 9
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 44
- 229920002367 Polyisobutene Polymers 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 18
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 17
- 229910003074 TiCl4 Inorganic materials 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 12
- 239000002841 Lewis acid Substances 0.000 claims description 11
- 150000007517 lewis acids Chemical class 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 3
- 239000012454 non-polar solvent Substances 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 95
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 67
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 238000006116 polymerization reaction Methods 0.000 description 35
- 229940050176 methyl chloride Drugs 0.000 description 26
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 20
- 239000012969 di-tertiary-butyl peroxide Substances 0.000 description 20
- 239000003999 initiator Substances 0.000 description 17
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 11
- 230000000977 initiatory effect Effects 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 150000001768 cations Chemical class 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000010550 living polymerization reaction Methods 0.000 description 8
- -1 poly(methyl methacrylate) Polymers 0.000 description 8
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 229920000098 polyolefin Polymers 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- NZIXICKPQWIFAU-UHFFFAOYSA-K bromo(dimethyl)alumane;dibromo(methyl)alumane Chemical compound C[Al](C)Br.C[Al](Br)Br NZIXICKPQWIFAU-UHFFFAOYSA-K 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000011877 solvent mixture Substances 0.000 description 6
- 239000011550 stock solution Substances 0.000 description 5
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 4
- 229910010165 TiCu Inorganic materials 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 229920001002 functional polymer Polymers 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012038 nucleophile Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- XBKBZMOLSULOEA-UHFFFAOYSA-L methylaluminum(2+);dibromide Chemical compound C[Al](Br)Br XBKBZMOLSULOEA-UHFFFAOYSA-L 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000569 multi-angle light scattering Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- UWKQJZCTQGMHKD-UHFFFAOYSA-N 2,6-di-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=N1 UWKQJZCTQGMHKD-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- MJMQIMYDFATMEH-UHFFFAOYSA-N 2-chloro-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)Cl MJMQIMYDFATMEH-UHFFFAOYSA-N 0.000 description 1
- KPJKMUJJFXZGAX-UHFFFAOYSA-N 2-chloropropan-2-ylbenzene Chemical compound CC(C)(Cl)C1=CC=CC=C1 KPJKMUJJFXZGAX-UHFFFAOYSA-N 0.000 description 1
- 229910015844 BCl3 Inorganic materials 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ZGMHEOLLTWPGQX-UHFFFAOYSA-M dimethylalumanylium;bromide Chemical compound C[Al](C)Br ZGMHEOLLTWPGQX-UHFFFAOYSA-M 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 238000004442 gravimetric analysis Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000011173 large scale experimental method Methods 0.000 description 1
- 238000010667 large scale reaction Methods 0.000 description 1
- 238000010552 living cationic polymerization reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/04—Monomers containing three or four carbon atoms
- C08F10/08—Butenes
- C08F10/10—Isobutene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/08—Butenes
- C08F110/10—Isobutene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
- C08F2810/30—Chemical modification of a polymer leading to the formation or introduction of aliphatic or alicyclic unsaturated groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
- C08F2810/40—Chemical modification of a polymer taking place solely at one end or both ends of the polymer backbone, i.e. not in the side or lateral chains
Definitions
- a method of synthesizing an endcapped polymer of the present invention comprises reacting in a solvent a polymer of fo ⁇ nula (I)
- the present invention provides a process to produce capped polyolefin polymers and the products obtained.
- this invention provides a method to "cap" a living polyolefin cation, typically a polyisoolefin cation, even more typically a living polyisobutylene cation (PIB + ), with a capping agent.
- PIB + living polyisobutylene cation
- the living polyolefin is any polyolefin with a terminal cationic group.
- these polyolefins are those that are made by living polymerization methods known to those of ordinary skill in the art.
- a preferred method for obtaining 100% capping is simply to wait.
- the time to wait will vary with the initiator, co-initiator and butadiene concentrations. With higher initiator concentrations the time is shorter, about 20 minutes, while lower initiator concentrations may require 10 hours to achieve 100% capping.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
La présente invention concerne une méthode de synthèse d'un polymère coiffé, qui comprend la réaction dans un solvant d'un polymère cationique vivant avec un diène conjugué éventuellement substitué au titre de réactif de coiffage, ledit solvant accélérant la terminaison par halogénation vis-à-vis de l'addition de molécules supplémentaires du diène conjugué, ce qui permet d'obtenir un polymère coiffé par un groupement halogéné.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66973905P | 2005-04-08 | 2005-04-08 | |
| US60/669,739 | 2005-04-08 | ||
| US67464905P | 2005-04-25 | 2005-04-25 | |
| US60/674,649 | 2005-04-25 | ||
| US67674505P | 2005-05-02 | 2005-05-02 | |
| US60/676,745 | 2005-05-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2006110647A1 true WO2006110647A1 (fr) | 2006-10-19 |
Family
ID=36764217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2006/013308 WO2006110647A1 (fr) | 2005-04-08 | 2006-04-07 | Réactions de coiffage en polymérisation cationique ; cinétique et utilité en synthèse |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US20060264577A1 (fr) |
| WO (1) | WO2006110647A1 (fr) |
Cited By (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007117566A3 (fr) * | 2006-04-07 | 2007-11-29 | Univ Massachusetts Lowell | Procede de preparation de copolymeres sequences par combinaison de polymerisations cationique et anionique |
| WO2008060333A1 (fr) * | 2006-11-17 | 2008-05-22 | University Of Massachusetts Lowell | Polymères hydrocarbonés fonctionnels et leur procédé de fabrication |
| WO2009027181A1 (fr) * | 2007-08-28 | 2009-03-05 | Basf Se | Procédé de production de composés à chaînes hydrocarbonées |
| WO2010009379A2 (fr) | 2008-07-18 | 2010-01-21 | Chevron Oronite Company Llc | Copolymères réalisés avec des polyoléfines à terminaison allyle et des réactifs acides insaturés, des dispersants utilisant ceux-ci, et des procédés de fabrication de ceux-ci |
| US7705090B2 (en) | 2004-08-20 | 2010-04-27 | Chevron Oronite Company Llc | Method for preparing polyolefins containing a high percentage of exo-olefin chain ends |
| US7709580B2 (en) | 2004-08-20 | 2010-05-04 | Chevron Oronite Company Llc | Method for preparation of polylefins containing exo-olefin chain ends |
| US7816459B2 (en) | 2005-12-30 | 2010-10-19 | Chevron Oronite Company Llc | Method for preparing polyolefins containing vinylidine end groups using polymeric nitrogen compounds |
| WO2011014665A2 (fr) | 2009-07-31 | 2011-02-03 | The University Of Southern Mississippi | Formation in situ de polyoléfines fonctionnelles à hydroxy terminal |
| US8013073B2 (en) | 2005-12-30 | 2011-09-06 | Chevron Oronite Company Llc | Method for preparing polyolefins containing vinylidine end groups using nonaromatic heterocyclic compounds |
| US8063154B2 (en) | 2008-06-24 | 2011-11-22 | The University Of Southern Mississippi | Preparation of exo-olefin terminated polyolefins via quenching with alkoxysilanes or ethers |
| US8133954B2 (en) | 2008-10-22 | 2012-03-13 | Chevron Oronite Company Llc | Production of vinylidene-terminated and sulfide-terminated telechelic polyolefins via quenching with disulfides |
| US8344073B2 (en) | 2009-01-16 | 2013-01-01 | The University Of Southern Mississippi | Functionalization of polyolefins with phenoxy derivatives |
| US8374704B2 (en) | 2009-09-02 | 2013-02-12 | Cardiac Pacemakers, Inc. | Polyisobutylene urethane, urea and urethane/urea copolymers and medical leads containing the same |
| US8394897B2 (en) | 2008-03-25 | 2013-03-12 | Chevron Oronite Company Llc | Production of vinylidene-terminated polyolefins via quenching with monosulfides |
| US8492491B2 (en) | 2010-06-10 | 2013-07-23 | Chevron Oronite Company Llc | Methods for producing telechelic polyolefins from terpene initiators |
| US8927660B2 (en) | 2009-08-21 | 2015-01-06 | Cardiac Pacemakers Inc. | Crosslinkable polyisobutylene-based polymers and medical devices containing the same |
| US8937134B2 (en) | 2010-06-14 | 2015-01-20 | The University Of Southern Mississippi | Vinyl ether end-functionalized polyolefins |
| US8962785B2 (en) | 2009-01-12 | 2015-02-24 | University Of Massachusetts Lowell | Polyisobutylene-based polyurethanes |
| US8969484B2 (en) | 2011-07-08 | 2015-03-03 | Chevron Oronite Company Llc | Methods of producing mono- and multi-functional polymers from terpene-based initiators |
| US9394390B2 (en) | 2013-02-07 | 2016-07-19 | The University Of Massachusetts | Coumarin-functionalized polyolefin and associated cyclodimerization products, preparation methods, and electronic devices |
| EP2994492A4 (fr) * | 2013-05-10 | 2017-01-04 | Henkel IP & Holding GmbH | Oligomères et polymères fonctionnels contenant du polyisobutylène |
| US9926399B2 (en) | 2012-11-21 | 2018-03-27 | University Of Massachusetts | High strength polyisobutylene polyurethanes |
| WO2019055984A1 (fr) | 2017-09-18 | 2019-03-21 | Chevron Oronite Company Llc | Dispersants de polyimide et leur procédés de fabrication et d'utilisation |
| WO2019055978A1 (fr) | 2017-09-18 | 2019-03-21 | Chevron Oronite Company Llc | Dispersants de polyoléfines et leur procédés de fabrication et d'utilisation |
| US10526429B2 (en) | 2017-03-07 | 2020-01-07 | Cardiac Pacemakers, Inc. | Hydroboration/oxidation of allyl-terminated polyisobutylene |
| US10835638B2 (en) | 2017-08-17 | 2020-11-17 | Cardiac Pacemakers, Inc. | Photocrosslinked polymers for enhanced durability |
| US11472911B2 (en) | 2018-01-17 | 2022-10-18 | Cardiac Pacemakers, Inc. | End-capped polyisobutylene polyurethane |
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| JP5137569B2 (ja) * | 2005-02-21 | 2013-02-06 | 三井化学株式会社 | ハイブリッドポリマーおよびその製造方法 |
| US7786217B2 (en) * | 2007-04-11 | 2010-08-31 | University Of Massachusetts Lowell | Organometallic-polyisomonoolefin block copolymers |
| CN102131530A (zh) | 2008-06-27 | 2011-07-20 | 心脏起搏器公司 | 聚异丁烯-氨基甲酸酯共聚物、聚异丁烯-脲共聚物和聚异丁烯-氨基甲酸酯/脲共聚物及含有这类共聚物的医疗器械 |
| US8552122B2 (en) | 2009-03-31 | 2013-10-08 | The University Of Southern Mississippi | Amine-terminated telechelic polymers and precursors thereto and methods for their preparation |
| US8644952B2 (en) * | 2009-09-02 | 2014-02-04 | Cardiac Pacemakers, Inc. | Medical devices including polyisobutylene based polymers and derivatives thereof |
| WO2012087480A1 (fr) | 2010-12-20 | 2012-06-28 | Cardiac Pacemakers, Inc. | Fil conducteur comportant un conducteur en polymère conducteur |
| JP2014525279A (ja) | 2011-08-12 | 2014-09-29 | カーディアック ペースメイカーズ， インコーポレイテッド | エレクトロスピニング法およびメルトブロー法を用いてデバイスをコーティングする方法 |
| US20150025608A1 (en) | 2013-07-22 | 2015-01-22 | Cardiac Pacemakers, Inc. | Lubricious, biocompatible hydrophilic thermoset coating using interpenetrating hydrogel networks |
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| US10465318B2 (en) | 2016-12-27 | 2019-11-05 | Boston Scientific Scimed Inc | Degradable scaffolding for electrospinning |
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| US7816459B2 (en) | 2005-12-30 | 2010-10-19 | Chevron Oronite Company Llc | Method for preparing polyolefins containing vinylidine end groups using polymeric nitrogen compounds |
| US8013073B2 (en) | 2005-12-30 | 2011-09-06 | Chevron Oronite Company Llc | Method for preparing polyolefins containing vinylidine end groups using nonaromatic heterocyclic compounds |
| WO2007117566A3 (fr) * | 2006-04-07 | 2007-11-29 | Univ Massachusetts Lowell | Procede de preparation de copolymeres sequences par combinaison de polymerisations cationique et anionique |
| WO2008060333A1 (fr) * | 2006-11-17 | 2008-05-22 | University Of Massachusetts Lowell | Polymères hydrocarbonés fonctionnels et leur procédé de fabrication |
| WO2009027181A1 (fr) * | 2007-08-28 | 2009-03-05 | Basf Se | Procédé de production de composés à chaînes hydrocarbonées |
| US8394897B2 (en) | 2008-03-25 | 2013-03-12 | Chevron Oronite Company Llc | Production of vinylidene-terminated polyolefins via quenching with monosulfides |
| US8063154B2 (en) | 2008-06-24 | 2011-11-22 | The University Of Southern Mississippi | Preparation of exo-olefin terminated polyolefins via quenching with alkoxysilanes or ethers |
| WO2010009379A2 (fr) | 2008-07-18 | 2010-01-21 | Chevron Oronite Company Llc | Copolymères réalisés avec des polyoléfines à terminaison allyle et des réactifs acides insaturés, des dispersants utilisant ceux-ci, et des procédés de fabrication de ceux-ci |
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| US8895672B2 (en) | 2008-10-22 | 2014-11-25 | Chevron Oronite Company Llc | Production of vinylidene-terminated and sulfide-terminated telechelic polyolefins via quenching with disulfides |
| US11174336B2 (en) | 2009-01-12 | 2021-11-16 | University Of Massachusetts Lowell | Polyisobutylene-based polyurethanes |
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| US8962785B2 (en) | 2009-01-12 | 2015-02-24 | University Of Massachusetts Lowell | Polyisobutylene-based polyurethanes |
| US9574043B2 (en) | 2009-01-12 | 2017-02-21 | University Of Massachusetts Lowell | Polyisobutylene-based polyurethanes |
| US8344073B2 (en) | 2009-01-16 | 2013-01-01 | The University Of Southern Mississippi | Functionalization of polyolefins with phenoxy derivatives |
| US9650449B2 (en) | 2009-01-16 | 2017-05-16 | The University Of Southern Mississippi | Functionalization of polyolefins with phenoxy derivatives |
| WO2011014665A2 (fr) | 2009-07-31 | 2011-02-03 | The University Of Southern Mississippi | Formation in situ de polyoléfines fonctionnelles à hydroxy terminal |
| US8927660B2 (en) | 2009-08-21 | 2015-01-06 | Cardiac Pacemakers Inc. | Crosslinkable polyisobutylene-based polymers and medical devices containing the same |
| US8903507B2 (en) | 2009-09-02 | 2014-12-02 | Cardiac Pacemakers, Inc. | Polyisobutylene urethane, urea and urethane/urea copolymers and medical leads containing the same |
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| US8937134B2 (en) | 2010-06-14 | 2015-01-20 | The University Of Southern Mississippi | Vinyl ether end-functionalized polyolefins |
| US8969484B2 (en) | 2011-07-08 | 2015-03-03 | Chevron Oronite Company Llc | Methods of producing mono- and multi-functional polymers from terpene-based initiators |
| US10562998B2 (en) | 2012-11-21 | 2020-02-18 | University Of Massachusetts | High strength polyisobutylene polyurethanes |
| US9926399B2 (en) | 2012-11-21 | 2018-03-27 | University Of Massachusetts | High strength polyisobutylene polyurethanes |
| US9394390B2 (en) | 2013-02-07 | 2016-07-19 | The University Of Massachusetts | Coumarin-functionalized polyolefin and associated cyclodimerization products, preparation methods, and electronic devices |
| EP2994492A4 (fr) * | 2013-05-10 | 2017-01-04 | Henkel IP & Holding GmbH | Oligomères et polymères fonctionnels contenant du polyisobutylène |
| US10526429B2 (en) | 2017-03-07 | 2020-01-07 | Cardiac Pacemakers, Inc. | Hydroboration/oxidation of allyl-terminated polyisobutylene |
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| WO2019055984A1 (fr) | 2017-09-18 | 2019-03-21 | Chevron Oronite Company Llc | Dispersants de polyimide et leur procédés de fabrication et d'utilisation |
| US11795247B2 (en) | 2017-09-18 | 2023-10-24 | The University Of Southern Mississippi | Polyolefin dispersants and methods of making and using thereof |
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